1. Field of the Invention
The present invention is concerned with novel compounds which are 2,3-dihalo-2,3-(disubstituted)propanoates. The present invention is also concerned with antimicrobial compositions containing these novel compounds as active ingredients, as well as with a method of inhibiting the growth of bacteria, yeast, fungi, and algae by contacting said bacteria, yeast, fungi, and algae with the novel compounds of the present invention. These novel antimicrobial compounds have a number of important industrial and agricultural applications.
As used herein, the term "antimicrobial" describes the killing of, as well as the inhibition of or control of the growth of bacteria, yeasts, fungi, and algae. A number of important industries can experience serious adverse effects from the activity of such bacteria and fungi on the raw materials which they employ, on various aspects of their manufacturing activities, or on the finished products which they produce. Such industries include the paint, wood, textile, cosmetic, leather, tobacco, fur, rope, paper, pulp, plastics, fuel, oil, rubber and machine industries. Important applications include: inhibiting the growth of bacteria in aqueous paints, adhesives, latex emulsions, and joint cements; preserving wood; preserving cutting oils; controlling slime-producing bacteria and fungi in pulp and paper mills and cooling towers; as a spray or dip treatment for textiles and leather to prevent mold growth; as a component of anti-fouling paints to prevent adherence of fouling organisms; as a hard surface disinfectant to prevent growth of bacteria and fungi on walls, floors, etc.; and in swimming pools to prevent algae. The control of bacteria and fungi in pulp and paper mill water systems which contain aqueous dispersions of papermaking fibers is especially important. The uncontrolled buildup of slime produced by the accumulation of bacteria and fungi causes offgrade production, decreased production due to breaks and greater cleanup frequency, increased raw material usage, and increased maintenance costs. The problem of slime deposits has been aggravated by the widespread use of closed white water systems in the paper industry.
Antimicrobial compounds are also utilized for agricultural applications, for example in preventing or minimizing the growth of harmful bacterial, yeast, and/or fungi on plants, trees, fruit seeds, or soil.
A particular application for which the antimicrobial compounds of the present invention have been found especially useful is in the protection of paint films from attack by fungi. Paint film fungicides which can preserve paint films from the deleterious effects of fungal attack which occur during weathering of the paint film have long been sought. Few, however, have been found due to the stringent requirements for such a successful paint film fungicide. Moreover, the ability to provide in-can preservative activity, as well as paint film protection, is also desirable. However, this additional characteristic is seldom seen in a paint film fungicide.
2. Brief Description of the Prior Art
Matt U.S. Pat. No. 3,608,084 describes halogenated aliphatic nitriles for controlling the growth of aerobacter bacteria in industrial water systems.
Grier, et. al., U.S. Pat. Nos. 3,833,731 and 3,877,922; and Harmetz, et. al. U.S. Pat. No. 3,873,597 describe 2-bromo-2-bromomethylglutaronitrile and related compounds and their use as antibacterial, antifungal, and algicidal agents.
Gershon, et. al., in J. Med. Chem. 20(4), 606-9 (1977), describe the antifungal properties of 2-bromo-3-fluorosuccinic acid esters.
Rader et al, British Pat. Spec. No. 1,424,943 describes .alpha.-(halomethyl)mandelonitrile microbiocides.
Tanaka et al., Japan. Kokai No. 75,123,828 (9-29-75), Chem. Ab. 84:39698t, disclose ethyl 2,3-dibromopropionate as an intermediate for preparing dithiolane herbicides and fungicides.
Motoyama et al., Sankyo Kenkyusho Nempo 23:233-44 (1971), Chem. Ab. 77:30239s, disclose 2,3-dichloropropionic acid as a herbicide.
However, there is no suggestion in any of the above references of the particular compounds of the present invention or their broad spectrum of antimicrobial activity.